NO306616B1 - Process for Preparation of the Left-Turn and Right-Turn Enantiomers of a 1 - [(4-Chlorophenyl) Phenylmethyl] -piperazine - Google Patents
Process for Preparation of the Left-Turn and Right-Turn Enantiomers of a 1 - [(4-Chlorophenyl) Phenylmethyl] -piperazineInfo
- Publication number
- NO306616B1 NO306616B1 NO990351A NO990351A NO306616B1 NO 306616 B1 NO306616 B1 NO 306616B1 NO 990351 A NO990351 A NO 990351A NO 990351 A NO990351 A NO 990351A NO 306616 B1 NO306616 B1 NO 306616B1
- Authority
- NO
- Norway
- Prior art keywords
- turn
- chlorophenyl
- ethyl
- enantiomers
- phenylmethyl
- Prior art date
Links
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title abstract 3
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 title 1
- -1 (3-methylphenyl)methyl Chemical group 0.000 abstract 7
- HIKIBGRLBOCOAZ-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)cyclohexa-2,4-dien-1-yl]methyl]piperazine Chemical class C1=CC(Cl)=CC=C1C1(CN2CCNCC2)C=CC=CC1 HIKIBGRLBOCOAZ-UHFFFAOYSA-N 0.000 abstract 2
- 206010020751 Hypersensitivity Diseases 0.000 abstract 2
- 230000007815 allergy Effects 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
Abstract
The use of levorotatory or dextrorotatory enantiomers of 1-(4-chlorophenyl)phenylmethylpiperazine derivatives (V) or their salts in medicines for the treatment of allergies, is new. The use of levorotatory or dextrorotatory enantiomers of 1-(4-chlorophenyl)phenylmethylpiperazine derivatives of formula (V) or their salts, in medicines for the treatment of allergies, is new: R = H, (3-methylphenyl)methyl, (4-tert-butylphenyl)methyl, 2-(2-hydroxyethoxy)ethyl, 2-(2-(hydroxyethoxy)ethoxy)ethyl, 2-(carbamoylethoxy)ethyl, 2-(methoxycarbonylmethoxy)ethyl or 2-(carboxymethoxy)ethyl.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB939305282A GB9305282D0 (en) | 1993-03-15 | 1993-03-15 | Enantiomers of 1-(4-chlorophenyl)phenylmethyl)-4-(4-methylphenyl)sulphonyl)piperazine |
Publications (3)
Publication Number | Publication Date |
---|---|
NO990351L NO990351L (en) | 1999-01-26 |
NO990351D0 NO990351D0 (en) | 1999-01-26 |
NO306616B1 true NO306616B1 (en) | 1999-11-29 |
Family
ID=10732080
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO940881A NO305908B1 (en) | 1993-03-15 | 1994-03-11 | Enantiomers of 1 - [(4-chlorophenyl) phenylmethyl] -4 - [(4-methylphenyl) sulfonyl] piperazine and process for their preparation |
NO990351A NO306616B1 (en) | 1993-03-15 | 1999-01-26 | Process for Preparation of the Left-Turn and Right-Turn Enantiomers of a 1 - [(4-Chlorophenyl) Phenylmethyl] -piperazine |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO940881A NO305908B1 (en) | 1993-03-15 | 1994-03-11 | Enantiomers of 1 - [(4-chlorophenyl) phenylmethyl] -4 - [(4-methylphenyl) sulfonyl] piperazine and process for their preparation |
Country Status (24)
Country | Link |
---|---|
US (17) | US5478941A (en) |
EP (3) | EP1413307A1 (en) |
JP (3) | JP3267434B2 (en) |
KR (1) | KR100322415B1 (en) |
AT (2) | ATE267185T1 (en) |
AU (1) | AU678426B2 (en) |
CA (2) | CA2443216C (en) |
DE (2) | DE69433802T2 (en) |
DK (1) | DK0617028T3 (en) |
ES (2) | ES2221262T3 (en) |
FI (3) | FI105477B (en) |
GB (1) | GB9305282D0 (en) |
GR (1) | GR3034340T3 (en) |
HK (1) | HK1024232A1 (en) |
HU (1) | HU219230B (en) |
NO (2) | NO305908B1 (en) |
NZ (1) | NZ260062A (en) |
PL (1) | PL178546B1 (en) |
PT (1) | PT617028E (en) |
RU (1) | RU2118320C1 (en) |
SG (1) | SG43683A1 (en) |
SI (2) | SI0617028T1 (en) |
TW (1) | TW237452B (en) |
ZA (1) | ZA941724B (en) |
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GB9305282D0 (en) * | 1993-03-15 | 1993-05-05 | Ucb Sa | Enantiomers of 1-(4-chlorophenyl)phenylmethyl)-4-(4-methylphenyl)sulphonyl)piperazine |
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US6384038B1 (en) | 1998-04-14 | 2002-05-07 | Sepracor Inc. | Methods and compositions using cetirizine in combination with leukotriene inhibitors or decongestants |
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US6432961B1 (en) * | 1998-08-18 | 2002-08-13 | Ucb S.A. | Method for preventing the onset of asthma |
WO2001040211A1 (en) * | 1999-11-30 | 2001-06-07 | EGIS Gyógyszergyár Rt. | A PROCESS FOR THE PREPARATION OF {2-[4-(α-PHENYL-p-CHLOROBENZYL)PIPERAZIN-1-YL]ETHOXY}ACETIC ACID AND NOVEL INTERMEDIATES THEREFOR |
JP2002249487A (en) | 2001-02-22 | 2002-09-06 | Sumitomo Chem Co Ltd | 4-(tert-butoxycarbonyl)piperazine derivative, optically active acid addition salt of the same, method for producing them and optically active 1-[(substituted phenyl)phenylmethylpiperazine which uses them |
US6977301B1 (en) | 2001-05-29 | 2005-12-20 | Ucb, S.A. | Process for preparing (S) and (R)—2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide |
US7199241B1 (en) | 2001-05-29 | 2007-04-03 | Ucb, S.A. | Process for preparing (S) and (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide |
US20040186112A1 (en) * | 2002-12-04 | 2004-09-23 | Dr. Reddy's Laboratories Limited | Polymorphic forms of dihydrochloride salts of cetirizine and processes for preparation thereof |
US20070014786A1 (en) * | 2003-03-20 | 2007-01-18 | Rinat Neuroscience Corp. | Methods for treating taxol-induced gut disorder |
US7577727B2 (en) * | 2003-06-27 | 2009-08-18 | Newisys, Inc. | Dynamic multiple cluster system reconfiguration |
KR100503443B1 (en) | 2004-02-02 | 2005-07-22 | 한림제약(주) | Processes for preparing an optically active cetirizine or its salt |
AU2006222298B2 (en) * | 2005-03-03 | 2011-02-24 | Ucb Farchim Sa | Pyroglutamate salts and their use in the optical resolution of intermediates for the synthesis of dextrocetirizine and levocetirizine |
HU227074B1 (en) * | 2005-12-08 | 2010-06-28 | Egis Gyogyszergyar Nyrt | An optically active carbamic acid derivative, method for producing the same and use as a pharmaceutical intermediate |
WO2008110586A2 (en) | 2007-03-12 | 2008-09-18 | Krka, Tovarna Zdravil, D.D., Novo Mesto | New process for the preparation of levocetirizine and intermediates thereof |
EP2167479B1 (en) | 2007-06-15 | 2013-09-11 | Symed Labs Limited | Process for preparation of substantially optically pure levorotatory and dextrorotatory enantiomers of cetirizine using novel intermediates |
US20090062305A1 (en) * | 2007-08-29 | 2009-03-05 | Protia, Llc | Deuterium-enriched cetirizine |
US20090082364A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched levocedtirizine |
KR101427100B1 (en) | 2007-10-23 | 2014-08-08 | 주식회사 씨트리 | Method for Preparing an Optically Active 1-[(4-chlorophenyl)phenylmethyl] -piperazine |
PL2062881T3 (en) | 2007-11-21 | 2011-07-29 | Synthon Bv | Process for making N-(diphenylmethyl)piperazines |
US7989623B2 (en) * | 2007-11-21 | 2011-08-02 | Synthon Bv | Process for making n-(diphenylmethyl)piperazines |
KR100954755B1 (en) * | 2007-12-17 | 2010-04-27 | 한미약품 주식회사 | Method for preparing r---1-[4-chloro-phenylphenyl-methyl]piperazine |
CA2724887A1 (en) * | 2008-06-02 | 2009-12-10 | Cipla Limited | Processes for the synthesis of levocetirizine and intermediates for use therein |
KR100998067B1 (en) | 2008-09-08 | 2010-12-03 | 주식회사 삼오제약 | A novel Bis1-[4-chlorophenylphenylmethyl]piperazine-2,3-Dibenzoyl tartarate intermediate salt and the method for isolating optically active 1-[4-chlorophenylphenylmethyl]piperazine using thereby |
US20100145049A1 (en) * | 2008-11-21 | 2010-06-10 | Jie Zhu | Process for making n-(diphenylmethyl)piperazines |
KR20120034627A (en) * | 2009-04-22 | 2012-04-12 | 액시킨 파마수티컬스 인코포레이티드 | Arylsulfonamide ccr3 antagonists |
CN101928223A (en) * | 2009-06-26 | 2010-12-29 | 华东理工大学 | Resolution method of (R)-(-)-4-chloro benzhydrylamine |
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CN104045607B (en) * | 2014-05-21 | 2016-04-13 | 丽珠医药集团股份有限公司 | A kind of purification process of cetrizine hcl |
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GB9305282D0 (en) * | 1993-03-15 | 1993-05-05 | Ucb Sa | Enantiomers of 1-(4-chlorophenyl)phenylmethyl)-4-(4-methylphenyl)sulphonyl)piperazine |
-
1993
- 1993-03-15 GB GB939305282A patent/GB9305282D0/en active Pending
-
1994
- 1994-03-08 TW TW083102003A patent/TW237452B/zh active
- 1994-03-08 US US08/207,096 patent/US5478941A/en not_active Expired - Lifetime
- 1994-03-09 EP EP04002438A patent/EP1413307A1/en not_active Withdrawn
- 1994-03-09 AT AT99109564T patent/ATE267185T1/en not_active IP Right Cessation
- 1994-03-09 SG SG1995002010A patent/SG43683A1/en unknown
- 1994-03-09 DK DK94870043T patent/DK0617028T3/en active
- 1994-03-09 DE DE69433802T patent/DE69433802T2/en not_active Expired - Fee Related
- 1994-03-09 EP EP94870043A patent/EP0617028B1/en not_active Expired - Lifetime
- 1994-03-09 SI SI9430329T patent/SI0617028T1/en unknown
- 1994-03-09 ES ES99109564T patent/ES2221262T3/en not_active Expired - Lifetime
- 1994-03-09 AT AT94870043T patent/ATE193889T1/en not_active IP Right Cessation
- 1994-03-09 PT PT94870043T patent/PT617028E/en unknown
- 1994-03-09 EP EP99109564A patent/EP0955295B1/en not_active Expired - Lifetime
- 1994-03-09 SI SI9430468T patent/SI0955295T1/en unknown
- 1994-03-09 ES ES94870043T patent/ES2147569T3/en not_active Expired - Lifetime
- 1994-03-09 DE DE69424893T patent/DE69424893T2/en not_active Expired - Fee Related
- 1994-03-10 FI FI941134A patent/FI105477B/en active
- 1994-03-10 NZ NZ260062A patent/NZ260062A/en not_active IP Right Cessation
- 1994-03-11 ZA ZA941724A patent/ZA941724B/en unknown
- 1994-03-11 NO NO940881A patent/NO305908B1/en not_active IP Right Cessation
- 1994-03-11 PL PL94302565A patent/PL178546B1/en not_active IP Right Cessation
- 1994-03-11 AU AU57771/94A patent/AU678426B2/en not_active Ceased
- 1994-03-11 HU HU9400727A patent/HU219230B/en not_active IP Right Cessation
- 1994-03-11 CA CA002443216A patent/CA2443216C/en not_active Expired - Fee Related
- 1994-03-11 CA CA002118859A patent/CA2118859C/en not_active Expired - Fee Related
- 1994-03-14 JP JP04254794A patent/JP3267434B2/en not_active Expired - Fee Related
- 1994-03-14 KR KR1019940005172A patent/KR100322415B1/en not_active IP Right Cessation
- 1994-03-14 RU RU94008618A patent/RU2118320C1/en active
-
1995
- 1995-06-05 US US08/460,844 patent/US5703082A/en not_active Expired - Fee Related
-
1997
- 1997-10-09 US US08/947,859 patent/US5792770A/en not_active Expired - Fee Related
-
1999
- 1999-01-26 NO NO990351A patent/NO306616B1/en not_active IP Right Cessation
- 1999-07-19 US US09/356,865 patent/US6436942B1/en not_active Expired - Fee Related
- 1999-08-16 FI FI991729A patent/FI105914B/en active
- 1999-08-16 FI FI991730A patent/FI105915B/en active
-
2000
- 2000-05-02 HK HK00102635A patent/HK1024232A1/en not_active IP Right Cessation
- 2000-09-06 GR GR20000402028T patent/GR3034340T3/en not_active IP Right Cessation
-
2001
- 2001-11-22 JP JP2001356849A patent/JP3880842B2/en not_active Expired - Fee Related
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2002
- 2002-05-10 US US10/141,933 patent/US20030105112A1/en not_active Abandoned
- 2002-06-06 US US10/162,576 patent/US20030105113A1/en not_active Abandoned
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2003
- 2003-03-12 US US10/385,522 patent/US20030204089A1/en not_active Abandoned
- 2003-10-07 US US10/679,376 patent/US20040072845A1/en not_active Abandoned
- 2003-12-02 US US10/724,640 patent/US20040122021A1/en not_active Abandoned
- 2003-12-02 US US10/724,611 patent/US20040122023A1/en not_active Abandoned
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2005
- 2005-04-15 US US11/106,528 patent/US20050182069A1/en not_active Abandoned
- 2005-04-15 US US11/106,456 patent/US20050182070A1/en not_active Abandoned
- 2005-04-15 US US11/106,613 patent/US20050176732A1/en not_active Abandoned
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2006
- 2006-06-16 US US11/453,986 patent/US20060229320A1/en not_active Abandoned
- 2006-06-16 US US11/453,987 patent/US20060229319A1/en not_active Abandoned
- 2006-07-17 US US11/487,331 patent/US20060252934A1/en not_active Abandoned
- 2006-09-29 JP JP2006266195A patent/JP2006342190A/en not_active Abandoned
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2007
- 2007-01-11 US US11/652,092 patent/US20070142400A1/en not_active Abandoned
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